For hotel suggestions we'll need to understand more about the type of accommodations you need. Are you hoping to all stay in one suite or room? Would two double or queen beds and a sofa bed work for you? Or are you thinking of two rooms? For everyone in one room, the options are more limited.
There are a number of hotels in Woburn that will take 3 adults + 2 kids in a suite. Expedia will show them. Since you'll be visiting Boston on weekdays, parking at many of the T stations will fill up early. www.mbta.com has info about parking facilities at stations and estimations of availability on a typical weekday. Just plan to get an early start (and you'll have commuter traffic)
For something closer to Boston, Hyatt Place Medford/Boston would be a good choice. They have a shuttle to Davis Square (where there is a T stop) and it's walking distance to Medford Square. $200 includes breakfast and free parking. 2 double beds and a sofa bed.
The more convenient you are to Boston, the less convenient you will be to road trips. But dealing with a longer drive for road trips is easier than dealing with a more complicated commute into Boston on a week day. I'd go with Medford.
Since you'll be going to Boston on a weekday, parking at many T stations fills up early. www.mbta.com has parking info and estimations about weekday availability. You may need to get an early start. Or you could just drive into Boston and pay to park there.